JP2015527400A5 - - Google Patents
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- JP2015527400A5 JP2015527400A5 JP2015531249A JP2015531249A JP2015527400A5 JP 2015527400 A5 JP2015527400 A5 JP 2015527400A5 JP 2015531249 A JP2015531249 A JP 2015531249A JP 2015531249 A JP2015531249 A JP 2015531249A JP 2015527400 A5 JP2015527400 A5 JP 2015527400A5
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- Prior art keywords
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- concentration
- glutathione
- composition
- oxidized
- Prior art date
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- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 105
- 108010024636 Glutathione Proteins 0.000 claims description 75
- 108010053070 Glutathione Disulfide Proteins 0.000 claims description 45
- YPZRWBKMTBYPTK-BJDJZHNGSA-N glutathione disulfide Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(=O)NCC(O)=O)CSSC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O YPZRWBKMTBYPTK-BJDJZHNGSA-N 0.000 claims description 45
- YPZRWBKMTBYPTK-UHFFFAOYSA-N oxidized gamma-L-glutamyl-L-cysteinylglycine Natural products OC(=O)C(N)CCC(=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(O)=O YPZRWBKMTBYPTK-UHFFFAOYSA-N 0.000 claims description 45
- 229960003180 glutathione Drugs 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 8
- 229960004308 acetylcysteine Drugs 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000001413 cellular effect Effects 0.000 claims description 4
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 claims description 4
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 claims description 4
- LNOVHERIIMJMDG-KTWAZNHYSA-N 2-[(6e,10e)-3-hydroxy-3,7,11,15-tetramethylhexadeca-6,10,14-trienyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LNOVHERIIMJMDG-KTWAZNHYSA-N 0.000 claims description 3
- FGYKUFVNYVMTAM-UHFFFAOYSA-N (R)-2,5,8-trimethyl-2-(4,8,12-trimethyl-trideca-3t,7t,11-trienyl)-chroman-6-ol Natural products OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-UHFFFAOYSA-N 0.000 claims description 2
- LTVDFSLWFKLJDQ-IEOSBIPESA-N 2-[(3r,7r,11r)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@](C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-IEOSBIPESA-N 0.000 claims description 2
- SFVAYPRWECRHTF-QRCIITMISA-N 2-[(6e,10e)-3-hydroxy-3,7,11,15-tetramethylhexadeca-6,10,14-trienyl]-6-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)(O)CCC1=CC(=O)C=C(C)C1=O SFVAYPRWECRHTF-QRCIITMISA-N 0.000 claims description 2
- OTXNTMVVOOBZCV-UHFFFAOYSA-N 2R-gamma-tocotrienol Natural products OC1=C(C)C(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-UHFFFAOYSA-N 0.000 claims description 2
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 claims description 2
- LTVDFSLWFKLJDQ-DKGMKSHISA-N alpha-Tocopherolquinone Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-DKGMKSHISA-N 0.000 claims description 2
- RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 claims description 2
- 229940066595 beta tocopherol Drugs 0.000 claims description 2
- FGYKUFVNYVMTAM-YMCDKREISA-N beta-Tocotrienol Natural products Oc1c(C)c2c(c(C)c1)O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CC2 FGYKUFVNYVMTAM-YMCDKREISA-N 0.000 claims description 2
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims description 2
- 235000010389 delta-tocopherol Nutrition 0.000 claims description 2
- FGYKUFVNYVMTAM-MUUNZHRXSA-N epsilon-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-MUUNZHRXSA-N 0.000 claims description 2
- OTXNTMVVOOBZCV-YMCDKREISA-N gamma-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CCc2c1 OTXNTMVVOOBZCV-YMCDKREISA-N 0.000 claims description 2
- 235000010382 gamma-tocopherol Nutrition 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 210000004698 lymphocyte Anatomy 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 210000002381 plasma Anatomy 0.000 claims description 2
- 210000002966 serum Anatomy 0.000 claims description 2
- 239000011590 β-tocopherol Substances 0.000 claims description 2
- 235000007680 β-tocopherol Nutrition 0.000 claims description 2
- 239000011723 β-tocotrienol Substances 0.000 claims description 2
- 235000019151 β-tocotrienol Nutrition 0.000 claims description 2
- FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 claims description 2
- 239000002478 γ-tocopherol Substances 0.000 claims description 2
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 claims description 2
- 239000011722 γ-tocotrienol Substances 0.000 claims description 2
- 235000019150 γ-tocotrienol Nutrition 0.000 claims description 2
- OTXNTMVVOOBZCV-WAZJVIJMSA-N γ-tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-WAZJVIJMSA-N 0.000 claims description 2
- 239000002446 δ-tocopherol Substances 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 102000014461 Ataxins Human genes 0.000 claims 2
- 108010078286 Ataxins Proteins 0.000 claims 2
- 208000001992 Autosomal Dominant Optic Atrophy Diseases 0.000 claims 2
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 2
- 208000024412 Friedreich ataxia Diseases 0.000 claims 2
- 208000014844 Mitochondrial neurogastrointestinal encephalomyopathy Diseases 0.000 claims 2
- 206010065271 Mitochondrial neurogastrointestinal encephalopathy Diseases 0.000 claims 2
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 208000010444 Acidosis Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000014644 Brain disease Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 1
- 208000027219 Deficiency disease Diseases 0.000 claims 1
- 208000016988 Hemorrhagic Stroke Diseases 0.000 claims 1
- 208000032382 Ischaemic stroke Diseases 0.000 claims 1
- 208000002569 Machado-Joseph Disease Diseases 0.000 claims 1
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 1
- 208000036572 Myoclonic epilepsy Diseases 0.000 claims 1
- 208000033716 Organic aciduria Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000036834 Spinocerebellar ataxia type 3 Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010043189 Telangiectasia Diseases 0.000 claims 1
- 230000007950 acidosis Effects 0.000 claims 1
- 208000026545 acidosis disease Diseases 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 208000014188 hereditary optic neuropathy Diseases 0.000 claims 1
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims 1
- 208000020658 intracerebral hemorrhage Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims 1
- 206010030875 ophthalmoplegia Diseases 0.000 claims 1
- 201000008152 organic acidemia Diseases 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 208000009056 telangiectasis Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261698431P | 2012-09-07 | 2012-09-07 | |
| US61/698,431 | 2012-09-07 | ||
| US201361792797P | 2013-03-15 | 2013-03-15 | |
| US61/792,797 | 2013-03-15 | ||
| PCT/US2013/058568 WO2014039862A1 (en) | 2012-09-07 | 2013-09-06 | Quinone derivatives for use in the modulation of redox status of individuals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015527400A JP2015527400A (ja) | 2015-09-17 |
| JP2015527400A5 true JP2015527400A5 (enExample) | 2016-10-20 |
| JP6393684B2 JP6393684B2 (ja) | 2018-09-19 |
Family
ID=49170942
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015531249A Expired - Fee Related JP6393684B2 (ja) | 2012-09-07 | 2013-09-06 | 個体のレドックス状態の調節において使用するためのキノン誘導体 |
| JP2015531266A Ceased JP2015533794A (ja) | 2012-09-07 | 2013-09-06 | 酸化ストレス障害を処置するためのベンゾキノン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015531266A Ceased JP2015533794A (ja) | 2012-09-07 | 2013-09-06 | 酸化ストレス障害を処置するためのベンゾキノン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US20150216820A1 (enExample) |
| EP (2) | EP2892516A1 (enExample) |
| JP (2) | JP6393684B2 (enExample) |
| CA (2) | CA2883882A1 (enExample) |
| HK (1) | HK1211872A1 (enExample) |
| WO (2) | WO2014039917A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006130775A2 (en) | 2005-06-01 | 2006-12-07 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomakers |
| JP5374162B2 (ja) | 2006-02-22 | 2013-12-25 | エジソン ファーマシューティカルズ， インコーポレイテッド | ミトコンドリア病および他の症状の処置のためのレドックス活性化治療の側鎖変異体およびエネルギーバイオマーカーの調節 |
| EP3456707B1 (en) | 2007-11-06 | 2020-04-15 | PTC Therapeutics, Inc. | 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases |
| EA023618B1 (ru) | 2008-01-08 | 2016-06-30 | Эдисон Фармасьютикалз, Инк. | Производные (гет)арил-п-хинона для лечения митохондриальных болезней |
| CA2717734A1 (en) | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc | 2-substituted-p-quinone derivatives for treatment of oxidative stress diseases |
| EP3827815B1 (en) | 2008-09-10 | 2023-09-06 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| TR201819154T4 (tr) | 2008-10-28 | 2019-01-21 | Bioelectron Tech Corp | Alfa-tokotrienol kuinone ve ara ürünlerini içeren bileşim. |
| WO2010126911A1 (en) | 2009-04-28 | 2010-11-04 | Edison Pharmaceuticals, Inc. | Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones |
| US9464016B2 (en) | 2011-06-14 | 2016-10-11 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| JP2014520894A (ja) | 2011-07-19 | 2014-08-25 | エジソン ファーマシューティカルズ， インコーポレイテッド | 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法 |
| CA2883882A1 (en) * | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Benzoquinone derivatives for treating oxidative stress disorders |
| US9868711B2 (en) | 2013-03-15 | 2018-01-16 | Bioelectron Technology Corporation | Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders |
| US9670170B2 (en) | 2013-03-15 | 2017-06-06 | Bioelectron Technology Corporation | Resorufin derivatives for treatment of oxidative stress disorders |
| US9296712B2 (en) | 2013-03-15 | 2016-03-29 | Edison Pharmaceuticals, Inc. | Resorufin derivatives for treatment of oxidative stress disorders |
| EP2970158B1 (en) | 2013-03-15 | 2019-02-20 | BioElectron Technology Corporation | Alkyl-heteroaryl substituted quinone derivatives for treatment of oxidative stress disorders |
| WO2014194292A1 (en) | 2013-05-31 | 2014-12-04 | Edison Pharmaceuticals, Inc. | Carboxylic acid derivatives for treatment of oxidative stress disorders |
| WO2015183963A2 (en) * | 2014-05-28 | 2015-12-03 | Stealth Peptides International, Inc. | Therapeutic compositions including redox-active parabenzoquinones and uses thereof |
| EP3233786B1 (en) | 2014-12-16 | 2022-03-16 | PTC Therapeutics, Inc. | Polymorphic and amorphous forms of (r)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
| EP3377179B1 (en) | 2015-11-19 | 2021-04-07 | Concert Pharmaceuticals Inc. | Deuterated epi-743 |
| EP3390377A1 (en) | 2015-12-16 | 2018-10-24 | BioElectron Technology Corporation | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| US10703701B2 (en) * | 2015-12-17 | 2020-07-07 | Ptc Therapeutics, Inc. | Fluoroalkyl, fluoroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
| JP2019501974A (ja) * | 2016-01-12 | 2019-01-24 | バイオエレクトロン テクノロジー コーポレイション | チオスルフェートレベルを増加させるためのまたは硫化水素レベルを低下させるためのトコフェロールキノン誘導体およびトコトリエノールキノン誘導体 |
| US10707531B1 (en) | 2016-09-27 | 2020-07-07 | New Dominion Enterprises Inc. | All-inorganic solvents for electrolytes |
| JP2018083799A (ja) | 2016-11-15 | 2018-05-31 | バイオエレクトロン テクノロジー コーポレイション | ２−置換アミノ−ナフト［１，２−ｄ］イミダゾール−５−オン化合物またはその製薬学上許容される塩 |
| WO2018129411A1 (en) | 2017-01-06 | 2018-07-12 | Bioelectron Technology Corporation | Aryl- and heteroaryl-resorufin derivatives for treatment of oxidative stress disorders and liver and kidney disorders |
| PL3866772T3 (pl) | 2018-10-17 | 2024-04-08 | Ptc Therapeutics, Inc. | 2,3,5-trimetylo-6-nonylocykloheksa-2,5-dieno-1,4-dion do hamowania i leczenia alfa-synukleinopatii, tauopatii i innych zaburzeń |
| WO2020252414A1 (en) | 2019-06-13 | 2020-12-17 | Ptc Therapeutics, Inc. | Naphthoquinone derivatives for treatment of oxidative stress disorders |
| KR20220078644A (ko) | 2019-10-04 | 2022-06-10 | 스텔스 바이오테라퓨틱스 인코포레이티드 | 미토콘드리아 질환 치료를 위한 바티퀴논의 퀴논-, 히드로퀴논- 및 나프토퀴논-유사체 |
| JP2023520462A (ja) | 2020-04-03 | 2023-05-17 | ステルス バイオセラピューティクス インコーポレイテッド | フリードライヒ運動失調症を含むミトコンドリア病の予防および／または治療のための組成物および方法 |
| JP7109705B2 (ja) * | 2020-08-07 | 2022-07-29 | 大鵬薬品工業株式会社 | 新規なシクロアルケノン化合物又はその塩 |
| KR20240032997A (ko) | 2021-07-08 | 2024-03-12 | 피티씨 테라퓨틱스, 인크. | 2,3,5-트리메틸-6-노닐사이클로헥사-2,5-디엔-1,4-디온을 포함하는 약제학적 조성물 |
| WO2023220365A1 (en) * | 2022-05-13 | 2023-11-16 | Virginia Tech Intellectual Properties, Inc. | Mitochondrial antioxidant treatment for cask-linked neurodevelopmental disorders |
| WO2024259130A1 (en) * | 2023-06-16 | 2024-12-19 | Ptc Therapeutics, Inc. | Methods for increasing vatiquinone plasma exposure with food |
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| DE3060165D1 (en) | 1979-03-08 | 1982-03-11 | Hoffmann La Roche | Process for the stereospecific preparation of compounds of the vitamin k1- and k2-series, as well as new starting materials for the process |
| JPS5640651A (en) | 1979-09-12 | 1981-04-16 | Takeda Chem Ind Ltd | Quinone compound and its preparation |
| US4393075A (en) | 1980-04-14 | 1983-07-12 | Takeda Chemical Industries, Ltd. | Quinone compounds and their use in suppressing the production of SRS-A in mammals |
| JPS57109739A (en) * | 1980-12-27 | 1982-07-08 | Takeda Chem Ind Ltd | Quinone compound and its preparation |
| JPS5910541A (ja) * | 1982-07-09 | 1984-01-20 | Takeda Chem Ind Ltd | キノン化合物 |
| EP0103361B1 (en) * | 1982-07-09 | 1986-01-29 | Takeda Chemical Industries, Ltd. | Quinone compounds, their production and use |
| JPS6143132A (ja) * | 1984-08-06 | 1986-03-01 | Takeda Chem Ind Ltd | キノン誘導体，その製造法およびそれを含んでなる医薬組成物 |
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2013
- 2013-09-06 CA CA2883882A patent/CA2883882A1/en not_active Abandoned
- 2013-09-06 WO PCT/US2013/058637 patent/WO2014039917A1/en not_active Ceased
- 2013-09-06 US US14/426,130 patent/US20150216820A1/en not_active Abandoned
- 2013-09-06 CA CA2883879A patent/CA2883879A1/en not_active Abandoned
- 2013-09-06 HK HK16100029.7A patent/HK1211872A1/xx unknown
- 2013-09-06 JP JP2015531249A patent/JP6393684B2/ja not_active Expired - Fee Related
- 2013-09-06 JP JP2015531266A patent/JP2015533794A/ja not_active Ceased
- 2013-09-06 EP EP13765880.3A patent/EP2892516A1/en not_active Withdrawn
- 2013-09-06 US US14/426,135 patent/US9629815B2/en not_active Expired - Fee Related
- 2013-09-06 EP EP13762705.5A patent/EP2892515A1/en not_active Withdrawn
- 2013-09-06 WO PCT/US2013/058568 patent/WO2014039862A1/en not_active Ceased
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2017
- 2017-04-10 US US15/483,933 patent/US20170209393A1/en not_active Abandoned